Bromobenzene → HCID 54718732, compound

HRID 549200Notes

Reaction equation

HRID 549200 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([O:12]CC)=O)[C:3]1=[O:15].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=1.BrC1C=CC=CC=1.COC(C)(C)C>CCCCCC>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:10]([C:4]2[C:3](=[O:15])[N:2]([CH3:1])[C:7]([CH3:8])=[CH:6][C:5]=2[OH:9])=[O:12])=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 153482-Amino-5-methylpyridineHCID 15413tert-Butyl methyl etherHCID 57619607Ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 54718732HCID 54718732, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

214 mg of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 101 mg of 2-amino-5-methylpyridine were added to 2.5 ml of bromobenzene and the mixture was stirred for 6.5 hours under heat refluxing condition. The reaction mixture was cooled to room temperature, and t-butyl methyl ether and n-hexane were added to the mixture. The resulting solid was collected by filtration, washed with t-butyl methyl ether and n-hexane, and dried to obtain N-(5-methyl-2-pyridyl)-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide

Workup

  1. temperatureunder heat
  2. temperaturerefluxing condition
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with t-butyl methyl ether and n-hexane
  5. customdried

Sources & evidence

ORD record
ord-8ff9469904a14f9e9df7164155cb6d4a
Source dataset
uspto-grants-2011_05
Patent number
US07943638B2

Reaction notes

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